(2S)-2-[(1R)-1-Iodo­ethyl]-1-(4-methyl­phen­ylsulfon­yl)pyrrolidine

The spectroscopically confused title compound, C₁₃H₁₈INO₂S, wrongly assigned previously, has been crystallographically identified. The relative configuration is the (R*,S*) form and not the (R*,R*) type as previously reported.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.046
• wR factor = 0.081
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           68.23
           From the CIF: _reflns_number_total               2702
           Count of symmetry unique reflns         1596
           Completeness (_total/calc)            169.30%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1106
           Fraction of Friedel pairs measured     0.693
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2005); program(s) used to solve structure: SIR97 (Altomare, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C13H18INO2S	F(000) = 752.00
Mr = 379.26	Dx = 1.704 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2ac 2ab	Cell parameters from 16475 reflections
a = 6.2297 (4) Å	θ = 3.6–68.2°
b = 12.2538 (8) Å	µ = 18.30 mm^−1
c = 19.3613 (13) Å	T = 93 K
V = 1477.99 (17) Å^3	Needle, colorless
Z = 4	0.15 × 0.03 × 0.02 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2426 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.099
ω scans	θmax = 68.2°
Absorption correction: multi-scan (Higashi, 1995)	h = −7→7
Tmin = 0.510, Tmax = 0.694	k = −14→14
17233 measured reflections	l = −22→23
2702 independent reflections

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2)] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.046	(Δ/σ)max = 0.002
wR(F^2) = 0.081	Δρmax = 1.47 e Å^−3
S = 1.04	Δρmin = −0.75 e Å^−3
2702 reflections	Absolute structure: Flack (1983), 1110 Friedel Pairs
166 parameters	Absolute structure parameter: −0.014 (9)
H-atom parameters constrained

Special details

Refinement. Refinement using all reflections. The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I(8)	0.23910 (6)	0.22564 (3)	0.93028 (2)	0.03997 (15)
S(9)	0.1133 (2)	0.24333 (11)	0.69763 (6)	0.0276 (3)
O(10)	0.2049 (6)	0.1366 (2)	0.70611 (17)	0.0290 (10)
O(11)	−0.1149 (5)	0.2558 (2)	0.69029 (18)	0.0301 (10)
N(1)	0.1813 (6)	0.3130 (3)	0.7653 (2)	0.0227 (11)
C(2)	0.4134 (8)	0.3052 (4)	0.7896 (2)	0.0244 (13)
C(3)	0.4589 (9)	0.4215 (4)	0.8157 (2)	0.0340 (16)
C(4)	0.3087 (8)	0.4927 (4)	0.7735 (3)	0.0357 (17)
C(5)	0.1053 (8)	0.4271 (4)	0.7712 (2)	0.0281 (14)
C(6)	0.4465 (9)	0.2137 (4)	0.8408 (2)	0.0336 (16)
C(7)	0.6784 (8)	0.2100 (4)	0.8638 (2)	0.0351 (16)
C(12)	0.2348 (8)	0.3038 (4)	0.6248 (2)	0.0236 (12)
C(13)	0.4386 (9)	0.2709 (4)	0.6041 (2)	0.0285 (15)
C(14)	0.5356 (9)	0.3218 (4)	0.5486 (2)	0.0287 (14)
C(15)	0.4396 (10)	0.4074 (4)	0.5144 (2)	0.0306 (15)
C(16)	0.2344 (11)	0.4404 (4)	0.5364 (2)	0.0321 (15)
C(17)	0.1323 (8)	0.3894 (4)	0.5902 (2)	0.0289 (15)
C(18)	0.5475 (10)	0.4634 (4)	0.4541 (2)	0.0422 (18)
H(2)	0.5065	0.2911	0.7485	0.029*
H(3A)	0.4271	0.4279	0.8657	0.041*
H(3B)	0.6106	0.4420	0.8076	0.041*
H(4A)	0.2850	0.5641	0.7962	0.043*
H(4B)	0.3663	0.5051	0.7265	0.043*
H(5A)	0.0200	0.4376	0.8138	0.034*
H(5B)	0.0167	0.4477	0.7308	0.034*
H(6)	0.4135	0.1434	0.8168	0.040*
H(7A)	0.7037	0.1431	0.8903	0.053*
H(7B)	0.7094	0.2736	0.8928	0.053*
H(7C)	0.7723	0.2108	0.8232	0.053*
H(13)	0.5105	0.2139	0.6279	0.034*
H(14)	0.6724	0.2970	0.5336	0.034*
H(16)	0.1651	0.4991	0.5134	0.039*
H(17)	−0.0072	0.4121	0.6039	0.035*
H(18A)	0.5234	0.5423	0.4571	0.063*
H(18B)	0.4869	0.4358	0.4107	0.063*
H(18C)	0.7020	0.4484	0.4552	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I(8)	0.0365 (3)	0.0498 (3)	0.0336 (2)	0.0036 (2)	0.0040 (2)	0.00610 (16)
S(9)	0.0249 (10)	0.0272 (8)	0.0306 (8)	−0.0023 (7)	−0.0008 (7)	−0.0001 (6)
O(10)	0.034 (2)	0.0200 (19)	0.033 (2)	−0.0020 (19)	−0.002 (2)	0.0003 (16)
O(11)	0.020 (2)	0.036 (2)	0.034 (2)	−0.0027 (18)	−0.001 (2)	0.0019 (19)
N(1)	0.025 (3)	0.022 (2)	0.021 (2)	0.002 (2)	−0.001 (2)	−0.002 (2)
C(2)	0.020 (3)	0.031 (3)	0.023 (3)	−0.005 (2)	−0.001 (2)	−0.002 (2)
C(3)	0.033 (4)	0.029 (3)	0.041 (3)	−0.005 (3)	−0.007 (3)	−0.000 (2)
C(4)	0.019 (4)	0.031 (3)	0.057 (4)	−0.007 (3)	−0.002 (3)	−0.004 (3)
C(5)	0.026 (4)	0.028 (3)	0.031 (3)	0.005 (3)	−0.005 (2)	0.003 (2)
C(6)	0.038 (4)	0.035 (3)	0.028 (3)	0.014 (3)	0.007 (3)	−0.004 (2)
C(7)	0.031 (4)	0.041 (4)	0.033 (3)	−0.002 (3)	0.009 (3)	0.004 (2)
C(12)	0.017 (3)	0.029 (3)	0.025 (2)	0.005 (3)	−0.008 (2)	−0.003 (2)
C(13)	0.028 (4)	0.028 (3)	0.030 (3)	−0.002 (3)	−0.004 (2)	0.005 (2)
C(14)	0.020 (3)	0.032 (3)	0.035 (3)	0.004 (3)	0.004 (3)	−0.008 (2)
C(15)	0.036 (4)	0.029 (3)	0.026 (3)	−0.001 (3)	−0.000 (3)	−0.004 (2)
C(16)	0.046 (4)	0.023 (2)	0.027 (3)	0.009 (3)	−0.010 (3)	−0.001 (2)
C(17)	0.023 (3)	0.036 (3)	0.029 (3)	0.006 (3)	−0.006 (2)	−0.001 (2)
C(18)	0.058 (5)	0.033 (3)	0.036 (4)	0.005 (3)	0.009 (3)	0.002 (3)

Geometric parameters (Å, º)

I(8)—C(6)	2.167 (5)	C(2)—H(2)	1.000
S(9)—O(10)	1.437 (3)	C(3)—H(3A)	0.990
S(9)—O(11)	1.437 (4)	C(3)—H(3B)	0.990
S(9)—N(1)	1.621 (4)	C(4)—H(4A)	0.990
S(9)—C(12)	1.763 (5)	C(4)—H(4B)	0.990
N(1)—C(2)	1.523 (6)	C(5)—H(5A)	0.990
N(1)—C(5)	1.481 (6)	C(5)—H(5B)	0.990
C(2)—C(3)	1.540 (7)	C(6)—H(6)	1.000
C(2)—C(6)	1.510 (7)	C(7)—H(7A)	0.980
C(3)—C(4)	1.518 (7)	C(7)—H(7B)	0.980
C(4)—C(5)	1.501 (7)	C(7)—H(7C)	0.980
C(6)—C(7)	1.513 (8)	C(13)—H(13)	0.950
C(12)—C(13)	1.391 (7)	C(14)—H(14)	0.950
C(12)—C(17)	1.400 (7)	C(16)—H(16)	0.950
C(13)—C(14)	1.381 (7)	C(17)—H(17)	0.950
C(14)—C(15)	1.377 (8)	C(18)—H(18A)	0.980
C(15)—C(16)	1.407 (9)	C(18)—H(18B)	0.980
C(15)—C(18)	1.513 (8)	C(18)—H(18C)	0.980
C(16)—C(17)	1.371 (7)
O(10)···C(3)^i	3.393 (6)	C(13)···H(14)^iii	3.248
O(10)···C(4)^i	3.528 (6)	C(13)···H(18C)^iii	3.273
O(10)···C(5)^ii	3.243 (6)	C(14)···H(14)^iii	3.126
O(10)···C(18)^iii	3.475 (6)	C(14)···H(17)^vii	3.238
O(11)···C(2)^iv	3.563 (6)	C(15)···H(7A)^viii	3.541
O(11)···C(4)^ii	3.514 (6)	C(15)···H(14)^iii	3.148
O(11)···C(13)^iv	3.249 (6)	C(16)···H(7A)^viii	2.887
O(11)···C(14)^iv	3.594 (6)	C(16)···H(14)^iii	3.231
I(8)···H(7A)^iv	3.570	C(17)···H(7A)^viii	3.294
I(8)···H(7B)^iv	3.430	C(17)···H(14)^iv	3.270
I(8)···H(7B)^v	3.430	C(17)···H(14)^iii	3.320
I(8)···H(7C)^iv	3.576	C(18)···H(5A)^ix	3.004
I(8)···H(18A)^i	3.463	H(2)···H(4A)^i	3.190
I(8)···H(18A)^vi	3.321	H(3A)···H(13)^viii	3.527
S(9)···H(4A)^ii	3.316	H(3A)···H(16)^vi	3.051
S(9)···H(7C)^iv	3.253	H(3A)···H(18A)^vi	3.338
S(9)···H(18B)^iii	3.136	H(3A)···H(18B)^vi	3.194
O(10)···H(3B)^i	2.661	H(3A)···H(18C)^x	3.262
O(10)···H(4A)^ii	3.179	H(3B)···H(5A)^vii	2.554
O(10)···H(4A)^i	3.300	H(3B)···H(5B)^vii	2.936
O(10)···H(4B)^i	3.382	H(3B)···H(6)^viii	3.452
O(10)···H(5A)^ii	2.837	H(3B)···H(18B)^x	3.538
O(10)···H(5B)^ii	2.959	H(3B)···H(18C)^x	3.366
O(10)···H(18B)^iii	2.783	H(4A)···H(6)^viii	3.043
O(10)···H(18C)^iii	3.292	H(4A)···H(7C)^viii	2.951
O(11)···H(2)^iv	2.649	H(4A)···H(13)^viii	2.674
O(11)···H(4A)^ii	2.591	H(4A)···H(18B)^vi	2.790
O(11)···H(7C)^iv	2.724	H(4B)···H(6)^viii	2.336
O(11)···H(13)^iv	2.677	H(4B)···H(7A)^viii	2.858
O(11)···H(14)^iv	3.349	H(4B)···H(7C)^viii	2.833
O(11)···H(18B)^iii	3.121	H(5A)···H(7B)^iv	3.182
N(1)···H(7C)^iv	3.052	H(5A)···H(7C)^iv	3.184
C(3)···H(5A)^vii	3.501	H(5A)···H(18A)^vi	2.798
C(4)···H(6)^viii	3.076	H(5A)···H(18B)^vi	2.436
C(4)···H(7C)^viii	3.303	H(5A)···H(18C)^vi	3.370
C(4)···H(13)^viii	3.501	H(7A)···H(16)^i	2.693
C(4)···H(18B)^vi	3.350	H(7A)···H(17)^i	3.406
C(5)···H(3B)^iv	3.167	H(7A)···H(18A)^i	3.501
C(5)···H(7C)^iv	3.513	H(7B)···H(18A)^x	3.067
C(5)···H(18B)^vi	3.234	H(13)···H(18B)^xi	3.568
C(6)···H(4B)^i	3.097	H(13)···H(18C)^iii	3.200
C(7)···H(4A)^i	3.585	H(14)···H(14)^iii	3.567
C(7)···H(4B)^i	3.072	H(14)···H(14)^xi	3.567
C(12)···H(14)^iii	3.330	H(14)···H(17)^vii	2.798
C(12)···H(18B)^iii	3.388	H(16)···H(18C)^iv	3.159
C(12)···H(18C)^iii	3.464	H(17)···H(18C)^iv	3.430
O(10)—S(9)—O(11)	120.1 (2)	H(3A)—C(3)—H(3B)	109.0
O(10)—S(9)—N(1)	106.5 (2)	C(3)—C(4)—H(4A)	111.1
O(10)—S(9)—C(12)	107.7 (2)	C(3)—C(4)—H(4B)	111.1
O(11)—S(9)—N(1)	106.4 (2)	C(5)—C(4)—H(4A)	111.1
O(11)—S(9)—C(12)	107.5 (2)	C(5)—C(4)—H(4B)	111.1
N(1)—S(9)—C(12)	108.2 (2)	H(4A)—C(4)—H(4B)	109.1
S(9)—N(1)—C(2)	117.7 (3)	N(1)—C(5)—H(5A)	111.0
S(9)—N(1)—C(5)	118.4 (3)	N(1)—C(5)—H(5B)	111.0
C(2)—N(1)—C(5)	109.8 (3)	C(4)—C(5)—H(5A)	111.0
N(1)—C(2)—C(3)	102.6 (4)	C(4)—C(5)—H(5B)	111.0
N(1)—C(2)—C(6)	112.2 (4)	H(5A)—C(5)—H(5B)	109.0
C(3)—C(2)—C(6)	116.5 (4)	I(8)—C(6)—H(6)	107.9
C(2)—C(3)—C(4)	104.0 (4)	C(2)—C(6)—H(6)	107.9
C(3)—C(4)—C(5)	103.2 (4)	C(7)—C(6)—H(6)	107.9
N(1)—C(5)—C(4)	103.8 (4)	C(6)—C(7)—H(7A)	109.5
I(8)—C(6)—C(2)	113.2 (3)	C(6)—C(7)—H(7B)	109.5
I(8)—C(6)—C(7)	109.6 (3)	C(6)—C(7)—H(7C)	109.5
C(2)—C(6)—C(7)	110.2 (4)	H(7A)—C(7)—H(7B)	109.5
S(9)—C(12)—C(13)	120.1 (3)	H(7A)—C(7)—H(7C)	109.5
S(9)—C(12)—C(17)	120.1 (4)	H(7B)—C(7)—H(7C)	109.5
C(13)—C(12)—C(17)	119.7 (4)	C(12)—C(13)—H(13)	120.2
C(12)—C(13)—C(14)	119.6 (5)	C(14)—C(13)—H(13)	120.2
C(13)—C(14)—C(15)	121.8 (5)	C(13)—C(14)—H(14)	119.1
C(14)—C(15)—C(16)	118.0 (5)	C(15)—C(14)—H(14)	119.1
C(14)—C(15)—C(18)	121.6 (5)	C(15)—C(16)—H(16)	119.3
C(16)—C(15)—C(18)	120.4 (5)	C(17)—C(16)—H(16)	119.3
C(15)—C(16)—C(17)	121.3 (5)	C(12)—C(17)—H(17)	120.2
C(12)—C(17)—C(16)	119.6 (5)	C(16)—C(17)—H(17)	120.2
N(1)—C(2)—H(2)	108.4	C(15)—C(18)—H(18A)	109.5
C(3)—C(2)—H(2)	108.4	C(15)—C(18)—H(18B)	109.5
C(6)—C(2)—H(2)	108.4	C(15)—C(18)—H(18C)	109.5
C(2)—C(3)—H(3A)	111.0	H(18A)—C(18)—H(18B)	109.5
C(2)—C(3)—H(3B)	111.0	H(18A)—C(18)—H(18C)	109.5
C(4)—C(3)—H(3A)	111.0	H(18B)—C(18)—H(18C)	109.5
C(4)—C(3)—H(3B)	111.0

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x, y−1/2, −z+3/2; (iii) x−1/2, −y+1/2, −z+1; (iv) x−1, y, z; (v) x−1/2, −y+1/2, −z+2; (vi) −x+1/2, −y+1, z+1/2; (vii) x+1, y, z; (viii) −x+1, y+1/2, −z+3/2; (ix) −x+1/2, −y+1, z−1/2; (x) −x+3/2, −y+1, z+1/2; (xi) x+1/2, −y+1/2, −z+1.